This lists songs that hit number one on the charts in the US during 1999. If a song spent nonconsecutive weeks at number one, the number of weeks for each occurrence at the top is shown in parenthesis.
| Date | Artist - Title | Weeks at #1 |
| November 29 1998 – January 9 1999 | R. Kelly and Celine Dion - I'm Your Angel | 6 |
| January 10 – 23 1999 | Brandy - Have You Ever? | 2 |
| January 24 – February 6 1999 | Britney Spears - ...Baby One More Time | 2 |
| February 7 – March 6 1999 | Monica - Angel Of Mine | 4 |
| March 7 – April 3 1999 | Cher - Believe | 4 |
| April 4 – May 1 1999 | TLC - No Scrubs | 4 |
| May 2 – June 5 1999 | Ricky Martin - Livin' La Vida Loca | 5 |
| June 6 – July 10 1999 | Jennifer Lopez - If You Had My Love | 5 |
| July 11 – 17 1999 | Destiny's Child - Bills, Bills, Bills | 1 |
| July 18 – 24 1999 | Will Smith feat. Dru Hill and Kool Mo Dee - Wild Wild West | 1 |
| July 25 – August 28 1999 | Christina Aguilera - Genie In A Bottle | 5 |
| August 29 – September 11 1999 | Enrique Iglesias - Bailamos | 2 |
| September 12 – October 2 1999 | TLC - Unpretty | 3 |
| October 3 – 16 1999 | Mariah Carey - Heartbreaker | 2 |
| October 17 1999 – January 8 2000 | Santana - Smooth | 12 |
15 different songs hit number one in the US during 1999.
Top 5 Songs of 1999
1: Cher - Believe
2: TLC - No Scrubs
3: Monica - Angel Of Mine
4: Whitney Houston feat Faith Evans - Heartbreak Hotel
5: Britney Spears - ...Baby One More Time
2: TLC - No Scrubs
3: Monica - Angel Of Mine
4: Whitney Houston feat Faith Evans - Heartbreak Hotel
5: Britney Spears - ...Baby One More Time